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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001493
Secondary Accession Numbers
  • HMDB01493
Metabolite Identification
Common Name3-Methylcrotonyl-CoA
Description3-Methylcrotonyl-CoA, also known as beta-methylcrotonyl-coenzyme A or dimethylacryloyl-CoA, belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, 3-methylcrotonyl-CoA is considered to be a fatty ester lipid molecule. 3-Methylcrotonyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Methylcrotonyl-CoA is an essential metabolite for leucine metabolism, is a substrate of 3-methylcrotonyl-CoA carboxylase (EC 6.4.1.4), and is a biotin-dependent mitochondrial enzyme in the catabolism of leucine (OMIM: 609010 ).
Structure
Data?1588356352
Synonyms
ValueSource
3,3-Dimethacrylyl-CoAChEBI
3,3-Dimethacrylyl-coenzyme AChEBI
3-Methylcrotonoyl-CoAChEBI
3-Methylcrotonyl-CoAChEBI
beta,beta-Dimethacrylyl-CoAChEBI
beta,beta-Dimethacrylyl-coenzyme AChEBI
Dimethylacryloyl-CoAChEBI
DMA-CoAChEBI
S-(3-Methyl-crotonoyl)-coenzym-aChEBI
S-(3-Methylcrotonoyl)-coenzyme AChEBI
b,b-Dimethacrylyl-CoAGenerator
β,β-Dimethacrylyl-CoAGenerator
b,b-Dimethacrylyl-coenzyme AGenerator
β,β-Dimethacrylyl-coenzyme AGenerator
3-Methylcrotonyl CoAHMDB
3-Methylcrotonyl-coenzyme AHMDB
Methylcrotonyl-CoAHMDB
Methylcrotonyl-coenzyme AHMDB
beta-Dimethylacrylylcoenzyme AHMDB
beta-Methylcrotonyl CoAHMDB
β-Dimethylacrylylcoenzyme AHMDB
β-Methylcrotonyl CoAHMDB
Chemical FormulaC26H42N7O17P3S
Average Molecular Weight849.64
Monoisotopic Molecular Weight849.157075088
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name3-methylcrotonyl-coa
CAS Registry Number6712-03-4
SMILES
CC(C)=CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1
InChI KeyBXIPALATIYNHJN-ZMHDXICWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker180.03330932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.57 g/LALOGPS
logP-0.33ALOGPS
logP-4.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity186.81 m³·mol⁻¹ChemAxon
Polarizability74.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+211.05230932474
DeepCCS[M-H]-209.39930932474
DeepCCS[M-2H]-243.45830932474
DeepCCS[M+Na]+218.17230932474
AllCCS[M+H]+259.532859911
AllCCS[M+H-H2O]+259.932859911
AllCCS[M+NH4]+259.132859911
AllCCS[M+Na]+259.032859911
AllCCS[M-H]-254.732859911
AllCCS[M+Na-2H]-259.032859911
AllCCS[M+HCOO]-263.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methylcrotonyl-CoACC(C)=CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N6308.1Standard polar33892256
3-Methylcrotonyl-CoACC(C)=CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N4301.0Standard non polar33892256
3-Methylcrotonyl-CoACC(C)=CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N6458.2Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcrotonyl-CoA 10V, Negative-QTOFsplash10-0002-0000000090-9d70f628f224bd5a36562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcrotonyl-CoA 20V, Negative-QTOFsplash10-00o1-9200202260-f6f406c6f46355e15d6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcrotonyl-CoA 40V, Negative-QTOFsplash10-004j-9001402220-413b1264cace3713a1142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcrotonyl-CoA 10V, Positive-QTOFsplash10-0udi-0100000290-61872b3e36018a4097d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcrotonyl-CoA 20V, Positive-QTOFsplash10-052r-0901002480-b271b8282bd3158fdbe72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcrotonyl-CoA 40V, Positive-QTOFsplash10-0006-0139000000-98db1fb5ea23ed71da702021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022652
KNApSAcK IDNot Available
Chemspider ID7828242
KEGG Compound IDC03069
BioCyc ID3-METHYL-CROTONYL-COA
BiGG IDNot Available
Wikipedia LinkMethylcrotonyl-CoA
METLIN IDNot Available
PubChem Compound9549326
PDB IDNot Available
ChEBI ID15486
Food Biomarker OntologyNot Available
VMH ID3MB2COA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wysocki SJ, Hahnel R: 3-Methylcrotonylglycine excretion in 3-hydroxy-3-methylglutaric aciduria. Clin Chim Acta. 1978 May 16;86(1):101-8. [PubMed:657530 ]

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:
ACADM
Uniprot ID:
P11310
Molecular weight:
46587.98
Reactions
Isovaleryl-CoA + FAD → 3-Methylcrotonyl-CoA + FADHdetails
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
IVD
Uniprot ID:
P26440
Molecular weight:
43055.325
Reactions
Isovaleryl-CoA + electron-transfer flavoprotein → 3-Methylcrotonyl-CoA + reduced electron-transfer flavoproteindetails
Isovaleryl-CoA + FAD → 3-Methylcrotonyl-CoA + FADHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
3-Hydroxyisovaleryl-CoA → 3-Methylcrotonyl-CoA + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:
ECHS1
Uniprot ID:
P30084
Molecular weight:
31387.085
Reactions
3-Hydroxyisovaleryl-CoA → 3-Methylcrotonyl-CoA + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
3-Hydroxyisovaleryl-CoA → 3-Methylcrotonyl-CoA + Waterdetails
General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
MCCC2
Uniprot ID:
Q9HCC0
Molecular weight:
61332.65
Reactions
Adenosine triphosphate + 3-Methylcrotonyl-CoA + Hydrogen carbonate → ADP + Phosphate + 3-Methylglutaconyl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MCCC1
Uniprot ID:
Q96RQ3
Molecular weight:
80472.45
Reactions
Adenosine triphosphate + 3-Methylcrotonyl-CoA + Hydrogen carbonate → ADP + Phosphate + 3-Methylglutaconyl-CoAdetails